How to Dress Like John F. Kennedy Jr.
As Ryan Murphy’s series revives the myth of JFK Jr., his enduring style of prep, polish, and downtown ease offers a timely blueprint for modern menswear
Ryan Murphy’s Love Story: John F. Kennedy Jr. & Carolyn Bessette has reignited a familiar cultural fixation. The nine-episode FX series revisits the romance between America’s closest approximation to royalty and the Calvin Klein publicist who became his wife.
More than 25 years after their deaths, Carolyn Bessette Kennedy and John F. Kennedy Jr. continue to function as aesthetic reference points. Carolyn’s minimalist polish has long been canonized. John’s style legacy is more complex. Rooted in Ivy League tradition but shaped by 1980s and 1990s New York, his wardrobe fused East Coast prep with athletic ease and a downtown sensibility.
Cap rotation
To dress like JFK Jr. is to understand that his appeal lay in how he wore his clothes. He embraced headwear before it became a celebrity signature, rotating between Yankees caps, newsboy styles, and even berets.
Everyday coats
Outerwear was central to his look. Bombers layered over turtlenecks, oversized trench coats, boxy leather jackets, and practical chore coats became staples.
He favored silhouettes that allowed movement, often wearing them slightly rumpled, sleeves pushed up, or collars turned against the wind. Frequently photographed on a bicycle or walking his dog, he projected a sense of motion that made even traditional pieces feel contemporary.
Relaxed suits
His tailoring followed a similar logic. In an era defined by power suits, John opted for boxier cuts that prioritized comfort over structure. Jackets skimmed rather than sculpted. Trousers were occasionally mismatched. He sometimes paired blazers with T-shirts, undercutting formality with ease.
Dark frames
Sunglasses completed the uniform. Classic Ray-Bans, tortoiseshell frames, and dark oval lenses appeared consistently in photographs. Eyewear functioned as both shield and signature in a period marked by intense media attention.
Casual knits
Knitwear offered another defining element. Crewnecks, quarter-zips, and ribbed turtlenecks balanced polish with approachability. He wore cashmere casually, favoring pieces that looked lived-in rather than preserved. The overall effect was aspirational without appearing curated, aligning with what is now described as quiet luxury.
Beyond the halo effect
It would be reductive to ignore the role of appearance in his legacy. JFK Jr.’s looks were central to his public image, and the so-called halo effect cannot be discounted. Yet physical attractiveness alone does not produce enduring style influence.
What distinguished him was a subtle irreverence. Stories of pairing formal tailoring with scuffed shoes, or even unconventional accessories, persist because they reflect a broader truth. He rarely appeared overworked.
As Ryan’s series demonstrates, the fascination extends beyond nostalgia. John and Carolyn’s aesthetic is frequently cited within our renewed interest in old money dressing, but Jr.’s contribution resists easy categorization. He absorbed the codes of American aristocracy and reframed them through the lens of a city in transition.
